Trifluoroacetic acid → HCID 131712844, compound

HRID 1703036Notes

Reaction equation

HRID 1703036 reaction equation
[NH:1]1[CH2:14][CH2:13][CH2:12][C@H:2]1[C:3]([NH:5][C@H:6]([C:9]([NH2:11])=[O:10])[CH2:7][OH:8])=[O:4].C(O)(C(F)(F)F)=O.CN1CCOCC1.[CH3:29][C:30]([O:33][C:34]([NH:36][C@H:37]([C:53]([OH:55])=[O:54])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:41][CH:40]=1)=[O:35])([CH3:32])[CH3:31].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:32][C:30]([O:33][C:34]([NH:36][C@H:37]([C:53]([OH:55])=[O:54])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:41][CH:40]=1)=[O:35])([CH3:29])[CH3:31].[NH:1]1[CH2:14][CH2:13][CH2:12][C@H:2]1[C:3]([NH:5][C@H:6]([C:9]([NH2:11])=[O:10])[CH2:7][OH:8])=[O:4]

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 71401659L-Prolyl-L-serinamide

Product 1

HCID 131712844HCID 131712844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.0 g (3.2 mmoles) H-Pro-Ser-NH2.CF3COOH (2) in 35 ml dimethylformamide is cooled at 0° C., then 0.36 ml (3.2 mmoles) N-methyl-morpholine are added, followed by 1.2 g (3.2 mmoles) Boc-Tyr (Bzl)-OH, 0.43 g (3.2 mmoles) 1-hydroxybenzotriazole, and 0.73 g (3.52 mmoles) dicyclohexylcarbodiimide. The reaction mixture is stirred for 1 hour at 0° C. and at room temperature overnight, then it is filtered, and evaporated in vacuo. The residue is dissolved in ethyl acetate and the solution washed successively with NaCl-saturated solutions of 1 M citric acid, 1 M NaHCO3, and water. The organic solution is dried over anhydrous Na2SO4 and the solvent removed in vacuo. The (3) product is recovered by crystallization from ethyl acetate-petroleum ether: 1.4 g, m.p. 115° C.; [α]D25 -22.9° (c=1, MeOH); RfA =0.20

Workup

  1. filtrationit is filtered
  2. customevaporated in vacuo
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution washed successively with NaCl-saturated solutions of 1 M citric acid, 1 M NaHCO3, and water
  5. dry with materialThe organic solution is dried over anhydrous Na2SO4
  6. customthe solvent removed in vacuo
  7. customThe (3) product is recovered by crystallization from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-610fc1468f124455807c18c6475f9f44
Source dataset
uspto-grants-1982_09
Patent number
US04350627

Reaction notes

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